10 Days of Writing, 10 Days Before I Attempt to Run a Sub-3 Hour Marathon, 2 Years After I Said I Would Never Become a Runner

Darren Tomasso
4 min readSep 29, 2022
📸 @dhash

For the next 10 days before the Chicago Marathon I am writing a brief article daily to give some insight on my approaches to training since I embarked on this marathon journey last year and what I have learned along the way. Plus it gives me something to focus my mind on while I’m tapering since I have a bit more time 😅.

Never did I ever see myself running a marathon but for as long as I remember I was a runner. A marathon was just never for me. I always had a love-hate relationship with running. While I ran cross country and track throughout middle school and winter track in high school, it was just a means to an end. Running was a form of cross training I had to do to get better at all the other sports I played. Did I love to run? Not really. Did I like how it helped me on the field or court? 100%

And then college happened where I fell into the “bro-science” mentality that “cardio kills gains.” I stopped running and my emphasis turned to competing in powerlifting (squat, bench, deadlift) and our yearly bodybuilding competition at Penn. More on this later, but these moments and what I learned developed how I approach health and wellness today (spoiler: having a certain aesthetic doesn’t make you healthy and I am happier and healthier now than ever before).

Ask me then if I ever saw myself running (let alone a marathon), and I probably would have laughed in your face and said “helllllllllllllll nah.”

But then I taught my first fitness class my junior year of college in 2015 and fell in love with the idea of training others. Penn had a huge mental health problem. But I saw the benefit fitness had on my mental health and decided to become certified and train at our athletics and recreation department to give an outlet for others to do the same. I was the only student trainer at the time and began learning from colleagues who have been in the field for years.

I began accepting a more holistic approach to health. (Again, much much more on this later).

2016–2017 I started training some runners of different levels and fell in love with the cross-training techniques and performance improvements they would start to recognize almost daily as they moved towards their long term goal (hence where my “WinYourDay” mindset was born). They would start to have a little less pain while running. They started to feel a bit stronger and see their miles get faster. This was so rewarding as a new trainer. I decided to break the traditional consulting and finance path Penn paved and moved to NYC in 2018 after graduation to venture towards a full time career in fitness.

I could see myself running a mile here and there to at least explore my new city.

Fast forward to 2019 working at SESSION where our studio manager at the time and now co-owner, Kat, asked if I would be down to work together on building out a class for runners. Still competing in powerlifting, I laughed and said, “I’m not doing any running.” Kat assured me that this would be a strength and mobility class for runners — no running involved! That year we launched the first non-running run club, Run Lab, and partnered with a bunch of different running clubs and brands like Rebook and Lululemon to train hundreds of runners throughout NYC all with different experiences and goals.

Fine, I’ll begrudgingly run more miles.

But despite training so many runners that year, when I was asked about my own marathon experience at the start of these sessions, I would always laugh it off and say, “never, I don’t think I’m built for that.” I felt like a poser since I never actually ran a marathon myself.

With gyms closed in 2020 due to the pandemic, I rekindled some joy with running and exploring the outdoors as the world around us became stagnant. Even my partner, Ashley, picked up running and trained for a half marathon trail race. I even ran a mile a day in September!

But late stage of the pandemic during the spring of 2021, I hurt my lower back due to a general lack of movement. Those weeks of pain and stiffness gave me time to take a step back, refocus and reevaluate goals. I had to really get serious with myself and ask, “What am I working towards? Why was I afraid to fully commit myself? Why can’t I run a marathon?”

With a heating pad on my lower back, I signed up for the 2021 Chicago Marathon. Alright, I have a 5 mile tempo run to complete. BRB.

Leave a comment or message me on Instagram to let me know your running or movement story!

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Darren Tomasso

Founder WinYourDay. Performance Trainer for the Everyday Athlete making Health & Wellness more Accessible. SESSION, “Plant-Forward,” Psych @uofpenn.